Publication
New Vinylation and Alkynylation Strategies with Hypervalent Iodine Reagents and Diazo Compounds
Related publications (164)
Novel Alkynylation Methods through the Combination of Hypervalent Iodine Reagents and Alkynyl-trifluoroborate Salts
The alkyne motif is a versatile functional group often encountered in organic chemistry. It can be involved in various transformations such as the alkyne-azide cycloaddition and has found widespread application in medicinal chemistry, chemical biology and ...
EPFL2024Editing Tetrasubstituted Carbon: Dual C–O Bond Functionalization of Tertiary Alcohols Enabled by Palladium-Based Dyotropic Rearrangement
Qian Wang, Jieping Zhu, Baochao Yang, Tristan Corentin Pierre Delcaillau
Many elegant asymmetric syntheses of enantioenriched tertiary alcohols have been developed, and both the transition metal-catalyzed and the radical-based peripheral functionalization of tertiary alcohols have attracted intensive research interest in recent ...
2024Synthesis and Applications of Ynimines and Enantioselective Total Synthesis of Artatrovirenol A
The first chapter of this thesis describe the development of a general synthesis of ynimines, an under-exploited motif in organic chemistry. In the presence of an inexpensive copper catalyst and 2,2'-biquinoline, reaction of easily accessible O-acyloximes ...
EPFL2023TiCl3-Mediated Reductive Cyclization of Tetrasubstituted Alkenes and Enol Esters Bearing a 2-Nitrophenyl Substituent
Indole is one of the most important heterocycles widely present in bioactive natural products, pharmaceuticals, agrochemicals and materials. Being easily accessible, the 2-nitrostyrenes are attractive starting materials for the indole synthesis and the Cad ...
EPFL2023Development of Hetero-Vinylbenziodoxolone Reagents for Applications in Synthetic Methodology and Biomolecule Functionalization
Among the numerous existing chemical motifs, alkenes, alkynes, enol ethers and enamides, with an unsaturated carbon-carbon bond, are versatile functional groups that are found in many natural products and bioactive compounds. They are widely used as valuab ...
EPFL2023Photocatalyzed [2σ + 2σ] and [2σ + 2π] Cycloadditions for the Synthesis of Bicyclo[3.1.1]heptanes and 5- or 6-Membered Carbocycles
Jérôme Waser, Matthew Wodrich, André Bossonnet
We report the use of photocatalysis for the homolytic ring-opening of carbonyl cyclopropanes. In contrast to previous studies, our approach does not require a metal cocatalyst or a strong reductant. The carbonyl cyclopropanes can be employed for both [2σ + ...
2023Diverting the 5-exo-Trig Oxypalladation to Formally 6-endo-Trig Fluorocycloetherification Product through 1,2-O/Pd(IV) Dyotropic Rearrangement
Qian Wang, Jieping Zhu, Jing Gong
Pd-catalyzed cyclizative functionalization of γ-hydroxyalkenes affords tetrahydrofuran derivatives via a key 5-exo-trig oxypalladation step. Herein, we report a palladium(II)-catalyzed, Selectfluor-mediated formal 6-endo-trig fluorocycloetherification of γ ...
2023Synthesis of hyperbranched polyarylethenes by consecutive C–H vinylation reactions
Kay Severin, Albert Ruggi, Anastasia Gitlina
A novel procedure for the synthesis of polyarylethenes is described. Consecutive C–H vinylation reactions of tetraphenylethene with a triphenylethenyl triazene give hyperbranched polyarylethenes of variable sizes. The vinylation reactions are mediated by a ...
2023Terminal Alkynes as One-Carbon Donors in [5+1] Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B
Qian Wang, Jieping Zhu, Rémi Hugo Lavernhe
Transition-metal-catalyzed [4+2] heteroannulation of alpha,beta-unsaturated oximes and their derivatives with alkynes has been developed into a powerful strategy for the synthesis of pyridines. It nevertheless lacks regioselectivity when unsymmetrically su ...
WILEY-V C H VERLAG GMBH2023Complexation Strategies towards Challenging Group 9 Metal Cyclopentadienyl Scaffolds
Cyclopentadienyl (Cp) metal complexes and their chiral counterparts (CpX) have enabled the development of challenging C-H activation transformations. While major progresses were made in developing new chiral CpX complexes and exploring their reactivity, th ...
EPFL2023